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89987-06-4 molecular structure
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{[(4-chlorophenyl)sulfanyl](phosphono)methyl}phosphonic acid

ChemBase ID: 1004
Molecular Formular: C7H9ClO6P2S
Molecular Mass: 318.608282
Monoisotopic Mass: 317.92835995
SMILES and InChIs

SMILES:
Clc1ccc(SC(P(=O)(O)O)P(=O)(O)O)cc1
Canonical SMILES:
Clc1ccc(cc1)SC(P(=O)(O)O)P(=O)(O)O
InChI:
InChI=1S/C7H9ClO6P2S/c8-5-1-3-6(4-2-5)17-7(15(9,10)11)16(12,13)14/h1-4,7H,(H2,9,10,11)(H2,12,13,14)
InChIKey:
DKJJVAGXPKPDRL-UHFFFAOYSA-N

Cite this record

CBID:1004 http://www.chembase.cn/molecule-1004.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
{[(4-chlorophenyl)sulfanyl](phosphono)methyl}phosphonic acid
IUPAC Traditional name
tiludronate
Brand Name
Skelid
Synonyms
Acide tiludronique [INN-French]
Acido tiludronico [INN-Spanish]
Acidum tiludronicum [INN-Latin]
Tiludronate disodium
Tiludronic acid
Tiludronic Acid Disodium Salt
Tiludronate
CAS Number
89987-06-4
PubChem SID
46505302
160964467
PubChem CID
60937

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB01133 external link
PubChem 60937 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 1.0278608  H Acceptors
H Donor LogD (pH = 5.5) -3.275569 
LogD (pH = 7.4) -3.4738543  Log P 1.3220819 
Molar Refractivity 65.1071 cm3 Polarizability 25.871422 Å3
Polar Surface Area 115.06 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.62  LOG S -1.66 
Solubility (Water) 6.97e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
-0.6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB01133 external link
Item Information
Drug Groups approved
Description Tiludronate is a bisphosphonate characterized by a (4-chlorophenylthio) group on the carbon atom of the basic P-C-P structure common to all bisphosphonates.
Indication For treatment of Paget's disease of bone (osteitis deformans).
Pharmacology Tiludronate is a first generation (non-nitrogenous) bisphosphonate in the same family as etidronate and clodronate. Tiludronate affects calcium metabolism and inhibits bone resorption and soft tissue calcification. Of the tiludronate that is resorbed (from oral preparation) or infused (for intravenous drugs), about 50% is excreted unchanged by the kidney. The remainder has a very high affinity for bone tissue, and is rapidly absorbed onto the bone surface.
Toxicity Based on the known action of tiludronate, hypocalcemia is a potential consequence of overdose. In one patient with hypercalcemia of malignancy, intravenous administration of high doses (800 mg/day total dose, 6 mg/kg/day for 2 days) was associated with acute renal failure and death.
Affected Organisms
Humans and other mammals
Biotransformation In vitro, tiludronic acid is not metabolized in human liver microsomes and hepatocytes. There is no evidence that tiludronate is metabolized in humans.
Absorption The mean oral bioavailability in healthy male subjects is 6% after an oral dose equivalent to 400 mg tiludronic acid administered after an overnight fast and 4 hours before a standard breakfast. In single-dose studies, bioavailability was reduced by 90% when an oral dose equivalent to 400 mg tiludronic acid was administered with, or 2 hours after, a standard breakfast compared to the same dose administered after an overnight fast and 4 hours before a standard breakfast.
Half Life Half-life in healthy subjects is 50 hours following administration of a 400 mg single oral dose. Half-life in pagetic patients is about 150 hours following administration of 400 mg tiludronate a day for 12 days. In patients with renal insufficiency (creatinine clearance between 11 and 18 mL per minute [mL/min]), half-life is 205 hours from plasma after administration of a single, oral dose equivalent to 400 mg tiludronate.
Protein Binding Approximately 90% bound to human serum protein (mainly albumin) at plasma concentrations between 1 and 10 mg/L.
Elimination The principal route of elimination of tiludronic acid is in the urine.
Clearance * renal cl=10 mL/min [IV administration of 20-mg dose]
References
Murakami H, Takahashi N, Sasaki T, Udagawa N, Tanaka S, Nakamura I, Zhang D, Barbier A, Suda T: A possible mechanism of the specific action of bisphosphonates on osteoclasts: tiludronate preferentially affects polarized osteoclasts having ruffled borders. Bone. 1995 Aug;17(2):137-44. [Pubmed]
Rogers MJ: New insights into the molecular mechanisms of action of bisphosphonates. Curr Pharm Des. 2003;9(32):2643-58. [Pubmed]
Sansom LN, Necciari J, Thiercelin JF: Human pharmacokinetics of tiludronate. Bone. 1995 Nov;17(5 Suppl):479S-483S. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Murakami H, Takahashi N, Sasaki T, Udagawa N, Tanaka S, Nakamura I, Zhang D, Barbier A, Suda T: A possible mechanism of the specific action of bisphosphonates on osteoclasts: tiludronate preferentially affects polarized osteoclasts having ruffled borders. Bone. 1995 Aug;17(2):137-44. Pubmed
  • • Rogers MJ: New insights into the molecular mechanisms of action of bisphosphonates. Curr Pharm Des. 2003;9(32):2643-58. Pubmed
  • • Sansom LN, Necciari J, Thiercelin JF: Human pharmacokinetics of tiludronate. Bone. 1995 Nov;17(5 Suppl):479S-483S. Pubmed
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